Diastereoselective construction of quaternary carbons directed via macrocyclic ring conformation:: Formal synthesis of (-)-mesembrine

被引：28

作者：

Arns, Steve ^{[1
]}

Lebrun, Marie-Eve ^{[1
]}

Grise, Christiane M. ^{[1
]}

Denissova, Irina ^{[1
]}

Barriault, Louis ^{[1
]}

机构：

[1] Univ Ottawa, Dept Chem, Ottawa, ON K1N 6N5, Canada

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2007年 / 72卷 / 24期

关键词：

D O I：

10.1021/jo701833v

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[Graphics] In this article, we report a highly diastereoselective new method for the generation of quaternary carbon centers through an anionic oxy-Cope/alkylation sequence where the diastereoselectivity is induced by the conformation of a macrocyclic tetrasubstituted enolate. The use of our methodology culminated in the formal total synthesis of (-)-mesembrine (34) in 11 steps from known starting materials.

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页码：9314 / 9322

页数：9

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